The AIM "SSL Handshake Failed" error is happening on 1.5.10 for me too, and the beta releases seem to require 10.7, which my iMac can't run.

I hope whatever the fix is can be rolled into a Snow Leopard-compatible release. Adium is by far my favorite chat client (I realize that in the dying world of people actually conversing and not just sending nudes that's sort of a "healthiest leper in the colony" compliment).

I am experiencing the same error with Adium when I try to connect."SSL Handshake Failed"

I am running a Mac Mini Core i5.My OS is Lion 10.7.5Build 11G63

My Adium verison is 1.5.10.4.

One day a month ago or so everything was fine.The next day, Adium wouldn't connect with that error.No changes were made to the OS from one day to the next.

I did a fresh install of Mac OS X Lion and installed all the updates and installed Adium of course, and I still got the same error.I then tried it on a fresh install of Mac OS X Mountain Lion with all the updates, and installed the same Adium and it WORKED!!!

On the Lion it doesn't work on, I looked in the Console log and found these two error messages...

I was wondering if somebody could tell me what these error numbers mean? Or point me in the right direction to find that out.

Also I realize the simplest solution would be just to upgrade my Lion to Mountain Lion, but that particular Mac Mini is my main Mac and I'm not going to do that. The fresh installs were done on other Mac Minis, just for testing purposes.

Oh, I also updated the Openssl library of Lion to the same version that Mountain Lion uses, from 0.9.8za to 0.9.8zg, but that didn't change anything. Same error.

I realize the error probably has something to do with a certificate expiring or something like that. I looked at the certificates in Keychain Access on both Lion and Mountain Lion and they are awfully similar. With nothing obvious like a certificate that has just expired.

And there you have it. If somebody could point me in the right direction, I would be most appreciative.

Ideally what I want to do is change the one thing on my Lion that is different from my Mountain Lion, to get Adium to connect again. Whether it be a setting someplace or coping a file from one os to the other. Yeah I know, the file coping fix method is probably frowned upon, but if it fixes it, I'll be happy.

Using the latest version of Adium, 1.5.10.4, I'm able to connect to AIM without a hitch.

For troubleshooting purposes, could those of you unable to connect please post a screenshot of your account settings? You can find them by opening Adium's preferences from the "Adium" menu, double-clicking your AIM account and then choosing the third tab called "Settings".

Below are my settings. I've tested connecting with each of the "Encryption" settings and all three work for me.

If I'm looking at the source code correctly, the error is coming from libpurple and they do their own SSL handshaking and not one of the other libraries (OpenSSL, etc).. It seems to be a generic SSL error and not anything specific to the protocol..

I was able to access the URL <https://api.oscar.aol.com/aim/startOSCARSession> from my older Mac 10.9.5 system without any certificate warning..

I finally figured out how to use Sourcetree with Lion 10.7.5. That was a bit a finagle. I wanted to see if I compiled Adium 1.5.10.4 would it work any better. I'd have to say no. Due to a compile error. The error is...

I also tried to compile it on Mountain Lion 10.8.5 with the same error. My Xcode version in both is 4.6.3.It would of been nice if it compiled as it would of been something to try. But this is a separate problem.

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For troubleshooting purposes, could those of you unable to connect please post a screenshot of your account settings?

Sure. Even though they are the same as yours...

I too tried all 3 encryption settings with no difference.

Here's an image of the actual error...

With my username removed by me.

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the error is coming from libpurple and they do their own SSL handshaking and not one of the other libraries (OpenSSL, etc)

I have not looked at the source code itself. Only tried to compile it. But I would have to disagree. As I am only getting the error from Lion 10.7.5 and not from Mountain Lion 10.8.5 with Adium 1.5.10.4 in both. I would think what ever is causing the error would have to be external to the Adium application itself. Now I'm not saying that an adjustment to Adium's source code couldn't fix the problem. That very well may be possible. But I just don't know.

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I don't think I mentioned this, this problem with Adium is happening when I use a AIM account. I have no other accounts with other protocols to try.

To get around this problem I have installed Pidgin using Macports. After some tweaking in the launching of the App to make it more Mac like (Instead of using the Terminal) it is working quite well.

shaosean wrote:Do you get any SSL error when going to that URL in Safari?

In Safari on Lion it does not work. The error i get is...

Safari can't open the page "https://api.oscar.aol.com" because Safari can'testablish a secure connection to the server "api.oscar.aol.com"

In Safari on Mountain Lion, where Adium does work, I get the same error.

I also have Firefox version 48.0.2 installed on both my Lion and Mountain Lion. And when I go to that url in Firefoxin both Lion and Mountain Lion, I get redirected to the aol home page. https://www.aol.com/

This might be an issue with the older operating systems not having support for the newer security certificates on the server.. You would probably need to compile a copy of OpenSSL (or whatever SSL library floats your boat) and then re-compile Adium to use it, instead of the system supplied one.. This is just guessing on my part though..